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The Saddest Breakup Songs Of All Time

Illustrated by Sydney Hass.

The Ronettes had it all wrong. The best part of breaking up is not the making up. That rarely happens, and when it does, it often leads to more breaking up.

No, the real pleasure in having your soul shredded by another human being comes in the days, weeks, months, or maybe even years of wallowing that follow. It’s a chance to wear pajama bottoms past noon and indulge in some serious self-reflection – the type that makes you a stronger, better person. This journey into the self can be scary, but luckily, generations of musicians have written songs to soundtrack the plunge.

What follows are the saddest (and therefore finest) breakup songs of all time. On this list you’ll find no TSwizz We’re Never Ever Getting Back Together” (too empowering) or Alanis Morissette You Oughta Know (too angry). These songs are plain and simple, rip-your-heart-out sad. Play ’em just loud enough to drown out the sobbing.

“How Do You Sleep?” The Stone Roses

Are you brimming over with slow-burning rage towards your former partner? Do you dream of elaborate revenge plans? Then blast this many-layered, biting song by one of England’s most criminally neglected rock bands, and sing: “Are my dreams your nightmare? / I hope they all come true.”

“Hey, That’s No Way To Say Goodbye,” Leonard Cohen

More than a breakup song, this is a song about a couple facing prolonged separation perhaps without the possibility of reunion. It’s profoundly romantic and will make you cry no matter the stage of a relationship you’re in.

It’s been two decades, and we haven’t been able to get the hook of this ’90s song about paralysis post-breakup out of our ears.

“Green Light” by Lorde

Lorde’s lyric, “I can get my things but I can’t let go,” might be the most succinct image of how hard it is to move on from a relationship.

“Smile” by Lily Allen

Lily Allen is the queen of snark said with a smile. “At first, when I see you cry / it makes me smile,” she sings.

“Tainted Love” by Gloria Jones

Everyone knows the cover of “Tainted Love” made popular by Soft Cell in the ’80s, but Gloria Jones Motown version sounds a bit more like a real breakup song.

“I Knew You Were Trouble,” Taylor Swift

Ah, but if she had listened to her gut, she wouldn’t have learned an important life lesson.

“Thinking Bout You” by Frank Ocean

With the line, “I’ve been thinking bout you / do you think about me still?” Frank Ocean reads our break-up ravaged insecurities.

“Torn” by Natalie Imbruglia

In which our favorite ’90s singer faces the disintegration of her relationship. Or, more specifically, the disintegration of her idea of the relationship. Disillusionment has never been so catchy.

“My Love Took Me Down to The River to Silence Me” by Little Green Cars

In this eerie folk anthem, a woman’s lover leaves her, and she’s left emotionally ravaged.”I’m still here waiting for you,” croons the lead singer of this band, inspired by the Irish musical tradition.

“Yesterday” by The Beatles

Some things, like the Beatles and Twilight Zone reruns, never get old. “Yesterday” is Paul McCartney at his most stripped-down, mopey, and vulnerable. The brilliance of the line, “Yesterday came suddenly,” grows on you.

“Lover You Should’ve Come Over” by Jeff Buckley

In this aching song, Buckley is mourning a relationship that ended because of his own wishy-washiness. Buckley doesn’t know how to stop wanting to be both free and committed. When he sighs, “And maybe i’m too young to keep good love from going wrong,” I can’t help but tear up -no matter the state of my heart.

“Hello” by Adele

If you haven’t cried while listening to “Hello,” what steel are you made of?

“Better in Time” by Leona Lewis

With a blend of hopefulness, nostalgia, and pain, Lewis sings of the light at the end of the breakup tunnel, when she’ll be all better -but will still miss her ex.

“So Long Marianne,” Leonard Cohen

Cohen looks back at his relationship with his real-life girlfriend, Marianne Jensen, with such poetic nostalgia. For when you know you have to leave -but how nice it would be if you could stay.

“Don’t Think Twice, It’s Alright,” Bob Dylan

Never has break-up sass been thrown so subtly and effectively. Dylan sings with the self-satisfied bite of the wronged party.

Stay, Lisa Loeb

Everyone’s favorite bespectacled over-thinker hit on something universal with the line, I think that I’m throwing, but I’m thrown. That’s what it’s like being in a bad relationship. The question of should I stay or should I go? isn’t always a binary yes-no kind of thing. Sometimes, it sends you down the kind of emotional rabbit hole Loeb goes into here, with winning results.

Photo: Courtesy of Geffen.

“Need You Now,” Lady Antebellum

In this unabashed cheese-fest, two exes say to us what they wish they were saying to each other. The couple seems a moment away from getting back together.

It Must Have Been Love, Roxette

Immortalized in Pretty Woman, It Must Have Been Love represents the perfect ratio of schlock to sentiment. In someone like Celine Dion’s hands, this would have been a complete disaster, but the Swedish duo of Marie Fredriksson and Per Gessle gaze off to where the water flows and where the wind blows without sounding like ’90s Disney characters.

Photo: Courtesy of EMI.

“If You See Her Say Hello” by Bob Dylan

Bob Dylan’s trying to play it casual in this ballad, but he’s dying to hear how his ex is doing.

All Cried Out, Lisa Lisa and Cult Jam

A year before freestyle queen Lisa Velez topped the charts with the gushy, lovey-dovey 1987 smash Head to Toe, she went the opposite route, putting foot to heart and pressing down hard. Don’t you know the hurt will cause an inferno? she sings, helpless against a fire that buckets of tears have failed to extinguish.

Photo: Courtesy of Columbia.

Don’t Turn Around, Ace of Base

Typically, neither crossover reggae hits nor songs by Swedish pop foursomes are known for being particularly sad. (When was the last time Sublime or Abba made you bawl?) For whatever reason, though, this moody summer jam – all about keeping a brave face while having your heart ripped out – has less bounce than a punctured beach ball.

Photo: Courtesy of Arista.

“Woke Up New” by the Mountain Goats

Sung in John Darnielle’s gravelly, raw voice, this song perfectly encapsulates the feeling of freedom and deep loneliness that occurs during the days following a breakup. “On the morning when I woke up without you for the first time / I felt free and I felt lonely and I felt scared,” the song opens.

The lyrics describe the sense of wandering through daily life with a phantom partner – not there in presence, but there in mind. Darnielle repeats, “What am I gonna do without you?” It’s the unanswerable question. He’ll do everything he did before, but after waking up new, nothing’s the same.

As the lyrics go, “I got ready for the future to arrive.” But for now, he’s here in the present, and nothing’s right at all.

Courtesy of 4AD

“The Heart Wants What It Wants” Selena Gomez

SelGo’s ballad tore us apart when it first debuted – mainly because it was presumably about Justin Bieber. (Sigh.) Like many great breakup songs, the tune details that moment when you’re teetering on the edge, deciding if the relationship has reached its end.

Also, it’s a great karaoke song.

“Stupid In Love,” Rihanna

When it comes to rousing anthems of love gone wrong, Rihanna reigns supreme. This 2009 single from her album Rated R emphasizes the idiocy involved in all failed relationships. Simply put: love is stupid. Relationships are stupid. We’re all stupid. (Stupid in love, one might say.)

“A Million Reasons,” Lady Gaga

Our Lady Gaga just went through a breakup of her own – she ended an engagement to actor Taylor Kinney while she was writing her newest album Joanne. Fittingly, the album is imbued with both mourning and a come-together rallying cry. The song “Million Reasons” narrates the harrowing decision to dump someone.

“You’re giving me a million reasons to let you go,” Gaga sings.

But, ultimately, we want to stay no matter what, right? The chorus ends with this unfortunate truth: “Baby, I just need one good one to stay.”

“Never Let Me Go,” Florence + The Machine

Florence Welch, with her melancholic croon, has always produced music that hits you in the proverbial feels. Even her happier songs, like “Dog Days Are Over,” hint at a deep sadness. “Never Let Me Go”is probably her weepiest production – or weep-inducing. Note: that isn’t to say the song is despondent. Somewhere in those hollow calls, there’s a hope for the future.

The sweeping chorus goes, “And the arms of the ocean are carrying me/And all this devotion was rushing out of me/ And the crashes are heaven for a sinner like me/ But the arms of the ocean delivered me.”

The ocean-as-lover metaphor works in two ways: the ocean can envelop you and make you feel surrounded. It can also swallow you whole. Weeping yet?

“Deep Blue Sea,” Grizzly Bear

The Grizzly Bear song keeps this melancholy tune simple with a repetitive structure – each verse reads the same line twice, building an incessant, obliging refrain. The song uses metaphor to allude to all that achey breakey pain, and it works.

The second verse croons: “Dig his grave darlin with a /silver spade/ Dig his grave darlin with a /silver spade.”

“Him” being, well, you know.

Photo: Courtesy of 4AD.

“Slow Dancing In A Burning Room,” John Mayer

John Mayer seems to specialize in the moony love song, the moony crush song, and, of course, the moony breakup song. There’s just something about that slow croon that scream melancholy romance. “Slow Dancing In A Burning Room” speaks to the final stages of a relationship – when you’re fully aware that this relationship ain’t headed anywhere good.

“This is the deep and dyin’ breath of/This love we’ve been workin’ on,” Mayer sings. In essence, the song is a eulogy for love lost, but it’s actually not all that plaintive. This is the breakup song that resolves the relationship turmoil, and it’s best for listening when you’re coming to terms with that newly single life.

“Gives You Hell” All-American Rejects

The pop-punk hit from 2008 is post-breakup bitching at its best. The refrain – “Hope it gives you hell” – summarizes our most juvenile sentiments toward an ex. It’s fun, angsty, and a great song to shout at your ex as they’re driving away in their getaway car or whatever.

“Truth be told, I miss you,” the All-American Rejects sing. But it’s a fake out! They continue, “And truth be told, I’m lyin’!”

The song is one giant, delicious middle finger to exes everywhere, and it’s oh-so-satisfying.

Photo: Courtesy of DGC – Interscope.

“Sober,” Childish Gambino

Gambino (Donald Glover) has always been a melancholy sort, crooning about the trials of the music industry and the perils of existence. “Sober” features CG’s plaintive falsetto singing about the need to be inebriated after a breakup.

He sings throughout the track, “And now that it’s over, I’ll never be sober.”

Yup, sounds about right.

“Seven Days Of Lonely,” I-Nine

The popular pop-rock song from the mid-aughts is quintessential shower singing. This is angsty lady pop at its best – call it a guilty pleasure if you want. Directed at a past lover, the lyrics are just plain tacky. (Which is exactly what we want post-breakup.)

Lead singer Carmen Keigans sings , “Tell me how I’m gonna make it, you’re the one I can’t forget/It’s like I’m running in slow motion in a nightmare that never ends.” Feel free to actually run in slow motion when you hear this part.

And then she puts it plainly: “God, I wish you could hold me through the seven days of lonely.”

“Cranes In The Sky,” Solange Knowles

From her third album A Seat At The Table, “Cranes” is about the desperate need to please, especially in the face of abject failure. Sound familiar? The title refers to man-made metal cranes used in construction. The lyrics read as a catalogue of various attempts at healing. Like a metal crane, the singer wants to construct a way of remaining ‘above’ the world’s maladies.

“I ran my credit card up,” Knowles sings. “Thought a new dress would make it better.” On a macro scale, the song is about pain in general – not just romance-induced ills – but the melancholy tone is the perfect complement for breakup blues.

“If I Ain’t Got You,” Alicia Keys

Alicia Keys was onto something with this track, from her (arguably) greatest album, The Diary of Alicia Keys. The R&B singer was soulful and subtle on this album, and this song’s simplicity made it a standout. Also: it was just really fun to sing (albeit offkey).

“Hand me the world on a silver platter, and what good would it be?” she asked. “Someone people want it all / But I don’t want nothing at all / If it ain’t you baby.”

“Gravity Don’t Pull Me,” Rostam

You know when the breakup is messy and sad and entirely your fault? Former Vampire Weekend bandmate Rosstam Batmanglij goes solo on this sad breakup track.

“And the worst things I ever did / was to this same boy I couldn’t help it,” he sings. “I messed things up / And it broke my heart.”

“Don’t Give Up On Me,” Solomon Burke

The singer famous for “Cry To Me” – you probably know it from Dirty Dancing – makes a true break up song. Soul singer Solomon Burke won a Grammy for the album, which borrows its title from this song.

“Hang in there baby, sooner or later,” Burke asks plainly. “I know I’ll get it right.”

“Missing,” The XX

The XX are really great at making songs about relationships. Not the breakup anthems or the Lemonade-style dizzying divorce solos – XX’s songs are about the nuances of every stage of a romance, even when it’s stalled.

“My heart is beating / In a different way,” they sing. “Been gone such a long time / I don’t feel the same.”

“Echoes of Silence,” The Weeknd

Before the lights and glamour of OVOXO, The Weeknd released Trilogy, an album of his mixtape songs that were floating around the internet. “Echoes of Silence” is one of the weepier tunes: Abel is asking his lover why she insists on hurting them both.

“It’s gonna end how you expected girl you’re such a masochist and I ask why,” Weeknd asks. But the woman is as emotionally ravaged as he is: “And you reply… / I like the thrill / Nothing’s gonna make me feel this real.” Ouch.

“These Arms Of Mine,” Otis Redding

No one does break up songs better than Otis Redding. “These Arms Of Mine” isn’t particularly weepy, but you can hear the longing in Redding’s deep voice. “These arms of mine, they are yearning / Yearning from wanting you / And if you would let them hold you / Oh, how grateful I will be,” the master of soul sings.

The lyrics are simple – Redding wishes his lover was back in his arms – but the way his voice ascends and drops is deeply moving.

“Take A Fall For Me,” James Blake Feat. RZA

James Blake and RZA play with the push-pull of a relationship that’s soured because of a struggle to commit. The song’s plot is simple enough: Blake/RZA are men who loved sleeping with a woman that wants more. When she decides to take another man’s proposal, their world shatters.

“What will become of me / If I can’t show my love to thee? / What will become of me?” RZA questions, his voice full of regret.

Photo: Courtesy of Republic Records.

“I Care,” Beyonc

Beyonc cares, y’all: “I told you how you hurt me, baby / But you don’t care / Now I’m crying and deserted, baby / But you don’t care.”

Bey’s vocals are piercing, and they should be. It hurts to be the only one putting in effort, caring about whether or not a relationship can be sustained. Once again, Beyonc says it better than anyone else ever could.

Photo: Courtesy of Parkwood.

“Not Gon’ Cry,” Mary J. Blige

In Waiting To Exhale, this song plays when Angela Bassett is deserted by her cheating husband. It might be the greatest break up song ever – the tempo feels like a desperate whine. MJB always delivers.

Photo: Courtesy of Arista.

Doing It Wrong, Drake

We live in a generation of not being love / And not being together, says the prophet Aubrey Drake Graham on this track. We’ve seen weepy Drake, lit Drake, Big Rings Drake. But this is the rapper’s magnum opus of sad breakup songs. Are you crying? We are.

Grizzly Bear co-lead singer Daniel Rossen supposedly wrote this song in a moment of frustration with his co-lead Ed Droste. You can feel the irritation in the deliberately slow pacing: “What would it take,” he repeats and over and over again, “to make you listen?”

Rossen and Droste never broke up – the bandmates still friendly – but the sentiment of being at your wits’ end in how to deal with someone who can’t feel your pain is real.

Photo: Courtesy of 4AD.

Marvins Room, Drake

Aubrey has a lot of emotions, and Marvins Room is when they’re the most raw. This is sad, regretful Drake: He’s addicted to thinking about the women that have abandoned him, and wants to tease them (and himself) with a drunken phone call. He’s made it big time, and wants to show off his success.

But what does he have to show for his fame? What has being 25 sitting on $25 mil brought? Late nights and loneliness. His ex has moved on with someone else, and he’s trapped in her memory. I’m just saying you could do better, he sings.

Photo: Courtesy of Young Money Entertainment.

“First Song for B,” Devendra Banhart

It’s hard to listen to this song without feeling an little bit of an ache. Devendra is in newly in love, and emboldened by it. “I wanna see you be the one who’s first light harbors in the new day / And see you settle into yourself,” he sings quietly. “And never be afraid.”

But love comes with the inevitable risk of disappointment and distress: “Please destroy me,” he begs.

Summertime, Vince Staples

Summertime begins and ends with a hook that echoes: This could be forever, baby, Vince says. His voice isn’t tender, but sad – the relationship he’s talking about could never be forever. He’s asking a girl to stay with him beyond summer, but knows that she won’t.

Summertime ’06 really is about that summer, and the crossroads it presented in the rapper’s life. In the album’s 20+ songs he zigs and zags between playful and precious. Summertime speaks to the latter: It’s love that keeps him home, but it’s the same love that’s tearing him apart.

My feelings told me love is real / But feelings known to get you killed / I feel as if I’m misconstrued / I spend my moments missin’ you, he says.

Photo: Courtesy of Def Jam.

White Ferrari, Frank Ocean

So Frank finally dropped the album. Blonde is marvellous, and White Ferrari is a sad-song highlight. Something about Frank Ocean’s voice feels intimate and close as he talks about a former love, before the song builds into layers and layers of songs and emotion.

Once Frank and his former lover could communicate without even speaking; now he only has his imagination of what they could have been. I care for you still and I will forever / That was my part of the deal, honest / We got so familiar, he sings.

Photo: Courtesy of Boys Don’t Cry.

How Can You Mend A Broken Heart, Al Green

Is there a song more suited to a particularly steamy, sad night? Is there a song more perfect for a bottle of whiskey and a long scroll through an ex’s engagement album? Al Green’s voice has that soft ’70s vibe, and the violins whine and whimper. Here’s your late night breakup song.

How can you mend this broken man? How can a loser ever win? Green asks, his voice sadly soulful. Somebody please help me mend my broken heart / And let me live again.

Photo: Courtesy of Motown/Universal Records.

“White,” Frank Ocean & Odd Future

While we wait for Boys Don’t Cry – whatever it is and whenever it arrives – this Frank Ocean deep cut is worth a revisit. Ocean sings a capella here, thinking out loud about love, heaven, and his fear of being swallowed into his own darkness.

“Could this be Earth? Could this be light?” Ocean asks. “Does this mean everything is going to be alright?” He’s brought into the bounty of the afterlife’s warmth and light, but still considers a former love. “But I’ll forget 23 like I forgot 17,” he says. “And I forget my first love, like you forget a daydream.”

Photo: Courtesy of Odd Future Records.

“A Message,” Kelela

Kelela’s voice sounds like something that drifted in from another planet. This song opens her EP Hallucinogen, and it sets the tone for the emotional, moody release.

On this track, Kelela sees everything with newfound clarity. She’s speaking to an ex-lover, revealing their relationship’s hardest truth: she has never satisfied him. A clean break is required. “You don’t even see me,” she sings, asking, “Are you even breathing?”

Photo: Courtesy of Warp.

Like You’ll Never See Me Again, Alicia Keys

By now we know that Alicia Keys is not – despite her efforts to the contrary – a soprano. But she had us fooled (and weeping) with “Like You’ll Never See Me Again.” She became an exciting artist to behold with this track, and its delicate R & B melody hasn’t aged. On the dreamy lullaby ‘Like You’ll Never See Me Again,’ [Keys] ponders whether she’ll be appreciated after a lover stops calling her name, wrote Rodney Dugue for Spin. A bonus: The song’s music video is equally heart-wrenching, even though it can never be forgiven for insinuating that it’s possible for Common to die.

Photo: Courtesy of J Records.

Caretaker, D.R.A.M. feat. SZA

D.R.A.M. revisits a highlight of Donnie Trumpet and the Social Experiment’s Surf, this time adding the perspective of SZA. The song is about two people who aren’t together anymore but still care deeply about one another: I’ll take care of you, I will / Even if I got a man now, SZA sings. These are friends from day one unable to untangle their lives: I’ma be there, ’cause I wasn’t there.

Photo: Courtesy of W.A.V.E. Recordings.

Gimme All Your Love, Alabama Shakes

Alabama Shakes is a good band, but it’s Brittany Howard’s voice that is central to making this song work. Her request – not just love me, but give me all the love you have – starts out as a whisper and grows into a growl. Maybe she’s singing about a punch-drunk love on its last legs, or a spark that’s dimmed.

Songs don’t have to be weepy and quiet to be sad. The great guitar riff around the track’s three-minute mark is like the push-pull of a toxic romance, a back-and-forth that continues (probably) despite a lover’s better judgment.

Photo: Courtesy of ATO Records.

“Bad Religion,” Frank Ocean

Obligatory friendly reminder that we, the people, are still waiting for Frank’s next album. (Cc: Frank Ocean, Bcc: Odd Future)

Could Bad Religion be the best track on an album that’s nearly perfect? No matter the answer, everything about this song is pitch-perfect on late-night desperation and loneliness. I can never make him love me, Ocean repeats. To recover from an unrequited love so barren, he might have to beg for a blessing from any god he can find.

Photo: Courtesy of Def Jam Recordings.

Plastic Bag, Drake & Future

If anybody know, I know, Drake mumbles at the song’s opening. We’re listening to What a Time to Be Alive Drake, the 6ix God himself, Drake punctuated by Future. This isn’t the open-wound Drake of albums past. On a record that manages to mimic a bit of the zeal and excess of Watch the Throne, Plastic Bag is a moment of real tenderness and sincerity.

Drake has a documented history of knowing and liking strippers. But this song isn’t about poles or thongs, it’s his way of sweetly appreciating the labor of these dancers, while also somberly observing the warped morality of his lavish lifestyle. Every syllable is weighed down by his guilt.

Photo: Courtesy of OVO Sound.

The Greatest, Cat Power

Cat Power’s bluesy voice drugs listeners into an easy melancholy. The musician (whose real name is Chan Marshall) expertly walks the line of beautiful but tortured. Once I wanted to be the greatest, she murmurs. No wind or waterfall could stall me / And then came the rush of the flood / Stars at night turned deep to dust. This song is about her complicated relationship with fame, but the soft rat-tat-tat of the drums makes it a great track for a cloudy-day cry.

Photo: Courtesy of Matador Records.

Foreground, Grizzly Bear

Grizzly Bear is deceptively simple. Upon the release of 2009’s Veckatimest, Pitchfork called Foreground masterful and muted. The song is anchored by a piano melody as it winds and twists its way into your wounds.

Take all evening, I’ll just be cleaning, frontman Edward Droste suggests. Take an evening to cry with this song. It’s the perfect background music to heal your woes head-on.

Photo: Courtesy of Warp.

End of the Road, Boyz II Men

The secret to life is that this is the greatest song ever written. The way it slowly builds from a regular ’90s ballad into a hymn of loneliness and sadness is mythic in that uniquely New Jack Swing way. It’s a deeply affecting breakup song but with a kind of the groupthink of wounded machismo: Why do you play with my heart, why do you play with my mind, the quartet croons.

Photo: Courtesy of Motown Records.

You Always Hurt The Ones You Love, Ryan Gosling

Remember Blue Valentine? Remember how it made you weep? Remember how the movie’s trailer still sometimes does? This soft Ryan Gosling melody is a major reason why.

The Mills Brothers made this song popular decades ago, but Gosling’s character isn’t a singer, so his voice cracks and stumbles over the lyrics. His uneven, tuneless sound is perfect. It’s slow and sad, and the movie’s ending raises its profile as a song ideal for a good weekend cry.

Photo: Courtesy of Lakeshore Records.

I’d Rather Go Blind, Beyonc

It goes without saying that this is an Etta James song – it’s always been an Etta James song. But Yonc’s cover for the 2008 drama Cadillac Records is spectacularly heartbreaking. And it might even be better.

The premise is simple enough: I’d rather be blind, boy, Bey sings, than to see you walk away from me. Her voice rises to match the song’s crescendo, and the effect is staggering. With this cover, Bey will have you missing your first relationship, your last relationship, and maybe even the train home.

Photo: Courtesy of Sony Legacy.

Higher, Rihanna

So, this isn’t technically a song about breaking up. But it’s still a song about missing someone, trying to move on, and feeling caught in the clutches of a relationship that has soured. In an interview with Vogue, RiRi herself compared it to a drunk voice mail: You know he’s wrong, and then you get drunk and you’re like, ‘I could forgive him. I could call him. I could make up with him.’ Just, desperate.

An added bonus: The song just sounds beautiful. [ Anti] is an intimate process, and Rihanna lets us see the fingerprints, the sweat stains, the fine lines, wrote Jenna Wortham for The New York Times Magazine. Her voice cracks as she sings ‘I hope I ain’t calling you too late’ over whining violins on ‘Higher,’ wobbling in a decidedly unpolished way. Seeing those seams is its own kind of beautiful, and a rarity in a pop world that tends toward polish and perfection.

Photo: Courtesy of Roc Nation.

Please, Please, Please Let Me Get What I Want, The Smiths

For breakups, bad days, and rainy afternoons, there are few groups more perfect than The Smiths. Please, Please, Please is gloomy, brooding, and oddly charming all at once. See the luck I’ve had can make a good man bad, Morrissey sings.

So what if 500 Days of Summer kind of made The Smiths cool for the Manic Pixie Dream Girl crowd? The song is just so easy to weep to.

Photo: Courtesy of Rough Trade Records.

Dreams, Kelsey Lu

Kelsey Lu’s voice reverberates with a bewitching frequency as she sings about loving a boy that’s bad for her. Lu’s voice drags into a guttural moan that’s deeply moving. I’m out drinking every night, hoping I’ll run into you, she sings. I know you’re no good, but I can’t get enough of you.

Lu is a new artist and an accomplished cello player. At 18, she ran away to music school and has been growing into an artist to watch since. Lu gently builds from distant, piercing intensity to something heavy and mournful, wrote Laura Snapes from Pitchfork.

Photo: Courtesy of Emmanuel Olunkwa.

Time Flies, Lykke Li

Lykke Li is weak and tired. Relationships are taxing, and breakups come with not only an emotional exhaustion, but a physical one too. The way her voice is barely a whisper, the way it fades in and out – her physical tiredness is palpable.

I get weak, I miss sleep, I get moody, the Swedish indie-pop singer croons. The song is called Time Flies, but it’s the perfect sad song because it shows exactly how time can drag.

Photo: Courtesy of LL Recordings.

Samson, Regina Spektor

Okay, so you used this song to get over your high school crush. And then you used it to get over your high school boyfriend. And then you used it just on long drives home in college. But this track is one of Regina Spektor’s greatest and most heartbreaking works of art.

The striking imagery – cutting a lover’s hair with blunt scissors, kissing in the morning light – is still there, and still just as moving. But Spektor also gets at a moving truth most sad love songs don’t talk about: The history books forgot about us and the Bible didn’t mention us, not even once.

Photo: Courtesy of Sire Records.

Sandcastles, Beyonc

Sometimes, losing love leads to more than just a breakup, it becomes a full-fledged crisis of faith. Lemonade isn’t a “breakup album,” but an album about the deepest recesses of loss: losing love, losing sanity, losing yourself as a relationship crumbles.

This track is a turning point on the album – it suggests the possibility of forgiveness – but you’re still left with these crippling lines: Bitch, I scratched out your name and your face / What is it about you that I can’t erase, baby? She’s not just talking about “Becky with the good hair.” This is a much more intimate loss.

Photo: Courtesy Parkwood/Columbia.

Lover’s Spit, Feist

This stripped-down version of the Broken Social Scene track bares all about unromantic sex and loveless physicality. Feist’s patchy vocals add to the song’s sad simplicity about lost connection: We’re all too busy smooching and swiping right to really engage with one another. You know it’s time that we grow old and do some shit. You won’t be crying over one breakup with this song; it preys on nostalgia for youthful romances and flirtatious flings, too.

Photo: Courtesy of Arts & Crafts.

Ne Me Quitte Pas, Nina Simone

For starters, the title is French for Don’t Leave Me. But you don’t have to understand another language to feel the deep unrest in Simone’s soul on this song. Simone – a truly distinct and talented vocalist (and concert pianist) – mourns her love, offering him rain and earth and everything in between. She’ll hide herself in his shadow after being rejected. I will dig the earth / Until after my death / To cover your body / With gold and light. Maybe don’t look up the French translation. Simone’s voice is enough to echo through your heart’s caverns.

Photo: Courtesy of Metro.

I’m Goin’ Down, Mary J. Blige

Mary J. Blige was in her 20s when she covered a less popular Rose Royce song from the 1970s for her 1994 My Life album. MJB croons about when sleep isn’t easy and everything is going wrong. Her tearful apology is the saddest song to come of the canon of heartbreaking ’90s R & B tracks.

Photo: Uptown/MCA Records.

“Skinny Love,” Bon Iver

Bon Iver, a.k.a. Justin Vernon, once told Pitchfork that “Skinny Love” is about when “you’re in a relationship because you need help, but that’s not necessarily why you should be in a relationship.” That anguish fills every note of this plaintive song. By the time Vernon wails, “And now all your love is wasted/ And then who the hell was I?” You’ll want to cry out along with him. Also, if Vernon’s notoriously bad enunciation means you can’t really understand what he’s saying, there’s always the beautiful Birdy cover.

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“Shiver,” Lucy Rose

We first got wind of Rose’s sweetly melancholy tune when it was employed during the Adam-Hannah split in season 4 of Girls. Since then, it’s been a go-to for when we’re feeling weepy. Rose doesn’t place the blame on her romantic partner for the split; she admits responsibility. But even though the breakup was mutual, she remains nostalgic for the good moments. “Shiver” is the perfect song for when you know you need to move on, but just can’t.

“A Case Of You,” Joni Mitchell

Joni Mitchell’s conversational, devastating song, describes what it’s like when a relationship is over but a connection to another person remains. “You’re in my blood like holy wine/ You taste so bitter and so sweet,” she sings. There are plenty of songs on Blue that will do the trick if you’re looking to wallow, but “A Case Of You” articulates what it’s like to a lose someone who has burrowed into your soul.

Photo: Courtesy of Warner Bros. Records.

Someone Like You, Adele

There’s a war going down inside Adele’s head. She wants her ex to be happy, and yet she finds herself wandering past his flat, hoping he’ll see her, remember the good times, and forget all about his new girl, who happens to be his wife. Never mind, I’ll find someone like you, she sings, though she, like Sinead, knows that nothing compares.

Photo: Courtesy of XL Recordings/Columbia.

Love Is Stronger Than Pride, Sade

Pride vs. love is like your JV high school basketball team vs. the 2012-13 Miami Heat. Sade knows all about the mismatch, and while she wishes she could hate this guy who’s wrecked her life, the affection she feels is quick and tenacious, like the triumvirate of LeBron James, Chris Bosh, and Dwayne Wade. All she can do is run out the clock and hope to rebuild next season.

Photo: Courtesy of Sony.

I Can’t Make You Love Me, Bonnie Raitt

Is it a breakup song if the people in question are still sharing a bed? In this all-time soul-crusher, the intimacy is purely physical, and as unfulfilling as that is, Bonnie will take it – for a little bit longer. Morning will come and I’ll do what’s right / Just give me till then to give up this fight, she sings, working up the strength to walk away. And I will give up this fight.

Photo: Courtesy of Capitol.

Nothing Compares 2 U, Sinead O’Connor

If you know the exact amount of time that’s elapsed since you got dumped, you’re in deep trouble. On this Prince-penned classic, we meet Sinead seven hours and 15 days after her love took a hike, and she’s still reeling. She’s even been to the see the doctor. Doc’s advice: Have some fun. Even in Ireland, the health-care system is whack.

Photo: Courtesy of Parlophone.

Song Cry, Jay-Z

Rappers have feelings, too. The thing about Jay is that he has trouble showing his, so in lieu of shedding actual tears, he aims to make this song cry. He does a decent job, though even as he opens his heart and apologizes to the girl he cheated on, he doesn’t quite ditch the macho posturing that might have made this tender mea culpa ring truer.

Photo: Courtesy of Roc-a-Fella Records.

Pictures of You, The Cure

Robert Smith has been writing intensely personal, moody songs of heartbreak pretty much since he founded The Cure in 1976. But this one is the most beautiful. Almost eight minutes long, “Pictures of You” finds Smith reflecting on memories of a person he loved, triggered by old photographs. Remembering you falling into my arms / Crying for the death of your heart / You were stone white, so delicate, lost in the cold, he sings. You were always so lost in the dark. For a Goth boy who is still married to his high school sweetheart, he sure knows how to capture the pain of lost love.

Photo: Courtesy of Elektra.

Crying, Roy Orbison

There’s nothing worse than bumping into your ex and having to pretend you’re not a total whimpering mess. Roy figures he pulls it off – You couldn’t tell that I’d been crying – and if he does, he’s a hell of an actor. In that signature opera-billy style of his, Orbison sings with a hurt not easily hidden.

Photo: Courtesy of WAX TIME.

Caroline, No, The Beach Boys

Originally titled Carol, I Know, this song became infinitely better when Brian Wilson misunderstood collaborator Tony Asher’s initial reading of the lyrics. The narrator in this song doesn’t know Jack. Where did your long hair go? he asks. Where is the girl I used to know? Could I ever find in you again things that made me love you so much then? If the bummed-out orch-pop backing is any indication, the answers to that last question is Brian, no.

Photo: Courtesy of Capitol.

You’ve Got to Hide Your Love Away, The Beatles

Everyone tells John Lennon he should suppress his feelings and go about his business, but this guy’s business was expressing his feelings. They come through in a big way on this transitional Beatles cut.

Photo: Courtesy of Capitol.

Lost Cause, Beck

Arguably the saddest song on Beck’s saddest album, this is the slow, strummy equivalent of waving a white flag. Poor Beck knows there’s nothing he can do to save this girl from herself, so he’s pulling his forces and signing whatever treaty he needs in order to escape with his sanity.

Photo: Courtesy of Interscope.

Nothing Better, The Postal Service

Selective memory is a the worst. The male character in this synth-pop duet figures there’d be nothing sweeter than marrying the girl who’s recently left him. Unfortunately, she’s prepared charts and graphs to remind him of why the good times weren’t that good. This is young love in the time of Excel.

Photo: Courtesy of Sub-Pop Records.

You Left Me Standing In the Doorway, Bob Dylan

Dylan waited until he was 56 to write one of the best lines of his career: Don’t know if I saw you, if I would kiss you or kill you. That, like the title, pretty much says it all, but then he goes one better: It probably wouldn’t matter to you anyhow. It’s a rascally line from a guy who’s wicked bummed but still pretty feisty.

Photo: Courtesy of Columbia.

The Heart Remains A Child, Everything But the Girl

In this song, vocalist Tracey Thorn bluntly asks a question that occurs too often during heartbreak: “Why don’t you love me?” If that seems like a simplistic inquiry, well, that’s sort of the point. This song perfectly expresses how we regress after heartbreak, and fall into our same, mopey patterns.

Photo: Courtesy of Virgin Records.

Stay, Rihanna ft. Mikky Ekko

Rih clears a little path through a hoarder’s den of messy feelings on this confusing piano ballad. Not really sure how I feel about it, she confesses, right before her duet partner, Mikky Ekko, sings the same line. These are two people who are completely wrong for each other, and when they join their voices on the line funny, you’re the broken one, but I’m the only one who needed saving, it’s like they’re both dishing blame and seeking salvation at the same time.

Photo: Courtesy of ISLAND-DEF JAM.

Again, Janet Jackson

When Janet hears her former boo is back in town, she goes off on a soul-searching journey that begins with wishful thinking (I’ll never fall in love with you again) and ends with acceptance (God knows I do love you again). The single-word title may be a predictor of how this story ends.

Photo: Courtesy of Virgin Records.

Almost Blue, Elvis Costello

There’s a girl here and she’s almost you, Elvis sings, weary like a lounge singer playing to a roomful of 2 a.m. drunks. He’s found a new romance that leaves him a little cold – almost blue – and that makes for one chilly-ass torch song.

Photo: Courtesy of Hip-O Records.

Heartless, Kanye West

At the risk of being melodramatic, Kanye dubs this the coldest story ever told. It’s the tale of two former lovers – presumably Yeezy and former fiance, Alexis Phifer – who’ve wronged each other and wound up bitter enemies. How could you be so Dr. Evil? he raps, too mentally spent to muster anything better than an Austin Powers joke.

Photo: Courtesy of Roc-A-Fella Records.

You Were Meant for Me, Jewel

If you ask Parks and Recreation protagonist Leslie Knope, there are few problems that can’t be solved by breakfast foods. Jewel might beg to differ. I got my eggs, I got my pancakes too / I got my maple syrup, everything but you, she sings, unwilling to accept her sugary a.m. feast as a substitute for the one that got away. Eventually, Jewel tells herself, he’ll realize they’re meant for each other. Until then, Mrs. Butterworth will have to pick up the slack.

Photo: Courtesy of Atlantic.

“The World Has Turned and Left Me Here, Weezer

Rivers Cuomo has it even worse than Robert Smith does in Pictures of You. On this Blue Album gem, the Weezer frontman is talking to wallet photos and losing his grip on reality. You laughed, enchanted by my intellect, he sings to his ex. Or maybe you didn’t. Either way, he won’t be adding any more smiley snapshots of this girl to his plastic sheath.

Photo: Courtesy of Geffen.

I Will Always Love You, Whitney Houston

That towering, thunderous, ground-shaking And I high note Whitney hits toward the end of this monster ballad makes total sense. Written by Dolly Parton, this is one of the most selfless love songs of all time, and before taking her leave of the man she knows she’s holding back, Whitney gets in one last show of dignity: an extended vowel sound people will be talking about until the end of time.

Photo: Courtesy of Sony Music Entertainment.

It’s Too Late, Carole King

It’s the sense of finality that makes this 1971 chart-topper such a killer. Something inside has died, and I can’t hide it, King sings, a little sad, a little relieved to no longer have to carry on a charade. And I just can’t fake it.

Photo: Courtesy of Sony.

Don’t Speak, No Doubt

Success must have been bittersweet for Gwen Stefani and Tony Kanal, punk-ska’s answer to Stevie Nicks and Lindsey Buckingham. No Doubt’s breakthrough 1996 single (and lone No. 1) is all about their breakup – an emotional earthquake Gwen clearly hadn’t recovered from the day she cut this vocal.

Photo: Courtesy of Interscope.

Are You Lonesome Tonight, Elvis Presley

In the famous spoken-word part, a truly miserable-sounding Elvis looks back on a failed relationship like a theater critic reviewing a play. Act one was great. Act two: not so much. Looking ahead to the act three, Elvis is only willing to entertain one possible ending. If you won’t come back to me, he says, then make them bring the curtain down.

Photo: Courtesy of RCA.

Without You, Mariah Carey

Talk about fresh wounds. I can’t forget this evening, or your face as you were leaving, sings Mariah, who’s coming to us mere hours after the breakup went down. She hasn’t had time to process things, so she’s feeling a little overdramatic. Hence that chorus: a show-stopping declaration of why life is no longer livable. In time, she’ll get over it, but for now, let her wail.

Photo: Courtesy of Sony.

Back to Black, Amy Winehouse

The references to puff and blow give this an air of druggy self-destruction that heightens the sadness, especially in light of Amy’s untimely death. Even without those lines, though, it’s a heavy song – a smoldering James Bond theme for an everyday story about a woman plummeting into darkness as her man goes back to his former girlfriend.

Photo: Courtesy of Universal Republic.

“Take a Bow,” Madonna

Taking a page out of the King’s playbook, Madonna uses theater as a metaphor for her latest heartbreak. “You deserve an award for the role that you played,” she tells the deceptive lover she’s finally wriggled free from. “No more masquerade.” Given that Madge used to be married to Sean Penn, the lesson here may be to onl